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PHENSERINE

CAS No.
101246-66-6
Chemical Name:
PHENSERINE
Synonyms
PHENSERINE;(-)-Phenserine;(3as-cis)-amate(ester;(-)-Eseroline phenylcarbamate;(-)-Eseroline phenylcarbamate;(-)-N-PHENYLCARBAMOYLESEROLINE;3-b)indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo(phenylcarb;1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol phenylcarbamate (ester);(3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol5-(N-phenylcarbamate);Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)-
CBNumber:
CB5731231
Molecular Formula:
C20H23N3O2
Molecular Weight:
337.42
MDL Number:
MFCD00672748
MOL File:
101246-66-6.mol
MSDS File:
SDS
Last updated:2023-06-08 09:02:49

PHENSERINE Properties

Melting point 151-152 °C
Boiling point 468.7±45.0 °C(Predicted)
Density 1.228±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility H2O: <2mg/mL
pka 13.05±0.70(Predicted)
form solid
color off-white
FDA UNII SUE285UG3S

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26
WGK Germany  3
RTECS  UY8586000
NFPA 704
0
2 0

PHENSERINE price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich P0111 Phenserine ≥98% (HPLC), solid 101246-66-6 25mg $144 2024-03-01 Buy
Sigma-Aldrich P0111 Phenserine ≥98% (HPLC), solid 101246-66-6 100mg $565 2024-03-01 Buy
Cayman Chemical 21060 Phenserine ≥98% 101246-66-6 5mg $36 2024-03-01 Buy
Cayman Chemical 21060 Phenserine ≥98% 101246-66-6 10mg $65 2024-03-01 Buy
Cayman Chemical 21060 Phenserine ≥98% 101246-66-6 25mg $134 2024-03-01 Buy
Product number Packaging Price Buy
P0111 25mg $144 Buy
P0111 100mg $565 Buy
21060 5mg $36 Buy
21060 10mg $65 Buy
21060 25mg $134 Buy

PHENSERINE Chemical Properties,Uses,Production

Uses

Phenserine is inhibitor of amyloid precursor protein (APP). Used in Alzheimer’s treatments.

Biological Activity

Physostigmine analog that inhibits acetylcholinesterase. Inhibits production of amyloid precursor protein (APP) and A β . Improves morris water maze performance of scopolamine-treated rats.

Enzyme inhibitor

This long-acting AChE inhibitor and A?42-lowering agent (FW = 337,42 g/mol; CAS 101246-66-6), also known as (–) -N-phenylcarbamoyl eseroline, is a carbamate analogue of eserine (or physostigmine) that inhibits acetylcholinesterase and is under active investigation for its potential in cholinomimetic therapy to reduce cognitive impairments associated with aging and Alzheimer's Disease. Phenserine is a potent and highly selective AChE inhibitor (IC50 = 22 nM), displaying 70x greater inhibitory action than observed with butyrylcholinesterase, or BChE (IC50 = 1560 nM), both in vitro and in clinical trials for treatment of Alzheimer's disease (1-5). Compared to physostigmine and tacrine, phenserine appears to be less toxic and robustly enhances cognition in animal models. In rats, phenserine achieves maximum acetylcholinesterase inhibition of 73.5% at 5 min, maintaining high and relatively constant inhibition for >8 hours. Phenserine decreased the levels of secreted b-amyloid precursor protein (b- APP) in the cerebrospinal fluid (CSF) of forebrain cholinergic system- lesioned rats, whereas DFP, a relatively non-specific cholinesterase inhibitor, failed to affect CSF levels of secreted b-APP. Such findings suggest that phenserine alters the induction of cortical b-APP mRNAs and increased levels of secreted b-APP in the CSF. Phenserine reduces Ab levels by regulating b-APP translation via a recently described iron regulatory element in the 5'-untranslated region of b-APP mRNA that was previously shown to be up-regulated in the presence of interleukin-1. Other dual AChE/A?42 inhibitors include: rivastigmine, ladostigil, asenapine, phenserine, amitriptyline, clomipramine, doxepin and desipramine. Posiphen, the better-tolerated (+) -enantiomer of phenserine, is devoid of anticholinesterase action, but represses translation of neural α- synuclein, a druggable target in the treatment of Parkinson Disease.

65166-97-4
101246-66-6
Synthesis of PHENSERINE from (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole

PHENSERINE Preparation Products And Raw materials

PHENSERINE Suppliers

Global( 38)Suppliers
Supplier Tel Email Country ProdList Advantage
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 19892 58
Nextpeptide Inc
+86-0571-81612335 +8613336028439 sales@nextpeptide.com China 19915 58
Aladdin Scientific
+1-+1(833)-552-7181 sales@aladdinsci.com United States 52927 58
Shanghai Eyougene biotechnology development co.LTD 021-52277372 13564545227 dom.sales@eyougene.com China 244 58
3B Pharmachem (Wuhan) International Co.,Ltd. 821-50328103-801 18930552037 3bsc@sina.com China 15848 69
Chemsky (shanghai) International Co.,Ltd 021-50135380 shchemsky@sina.com China 15421 60
Hangzhou Yuhao Chemical Technology Co., Ltd 0571-82693216 info@yuhaochemical.com China 9394 52
EMMX Biotechnology LLC 888-539-0666 info@emmx.com United States 8449 60
Shanghai EFE Biological Technology Co., Ltd. 021-65675885 18964387627 info@efebio.com China 9709 58
Aikon International Limited 025-66113011 18112977050 sales01@aikonchem.com China 16028 58
(3as-cis)-amate(ester 3-b)indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo(phenylcarb (-)-N-PHENYLCARBAMOYLESEROLINE PHENSERINE (3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol5-(N-phenylcarbamate) 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol phenylcarbamate (ester) (-)-Eseroline phenylcarbamate Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)- (-)-Phenserine (-)-Eseroline phenylcarbamate 101246-66-6